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Synthesis 2009(2): 165-193
DOI: 10.1055/s-0028-1083300
DOI: 10.1055/s-0028-1083300
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
Selected Synthetic Strategies to Spirocyclics
Weitere Informationen
Received
19 September 2008
Publikationsdatum:
09. Januar 2009 (online)
Publikationsverlauf
Publikationsdatum:
09. Januar 2009 (online)
Abstract
The design and synthesis of spirocycles is a challenging task because it involves the creation of a quaternary center, which itself is considered to be one of the most difficult tasks among synthetic transformations. Some recent approaches based on metathesis, cycloaddition and transition-metal-mediated transformations to spirocycles are described here.
1 Introduction
2 Scope of the Review
3 Alkylation Methods
4 Transition-Metal-Based Approaches
5 Rearrangement-Based Approaches
6 Ring-Expansion Method
7 Ring-Contraction Method
8 Photochemical Approaches
9 Ring Closure of Geminally Disubstituted Compounds
10 Cycloaddition Tactics
11 Other Cyclization Methods
12 Metathesis Approaches
13 Pauson-Khand Reaction
14 Conclusions and Future Prospects
Key words
spiro compounds - metathesis - Diels-Alder reactions - domino reactions - Suzuki coupling - radical reactions - ring closure
- For selected examples related to fredericamycin synthesis, see:
-
1a
Kelly TR.Ohashi N.Armstrong-Chong RJ.Bell SH. J. Am. Chem. Soc. 1986, 108: 7100 -
1b
Mehta G.Subrahmanyam D. Tetrahedron Lett. 1987, 28: 479 -
1c
Rama Rao AV.Singh AK.Venkateswara Rao B.Reddy KM. Tetrahedron Lett. 1993, 34: 2665 -
1d
Kita Y.Higuchi K.Yoshida Y.Iio K.Kitagaki S.Akai S.Fujioka H. Angew. Chem. Int. Ed. 1999, 38: 683 -
1e
Kita Y.Higuchi K.Yoshida Y.Iio K.Kitagaki S.Ueda K.Akai S.Fujioka H. J. Am. Chem. Soc. 2001, 123: 3214 -
2a
Marshall JA. Prog. Chem. Nat. Prod. 1974, 31: 283 -
2b
Heathcock CK.Graham SL.Pirrung Palvac F.White CT. Total Synthesis of Natural Products Vol. 11:ApSimon J. John Wiley; New York: 1983. p.264-314 -
2c
.
Studies in Natural Products Chemistry
Elsevier;
Oxford:
1989.
-
2d
Spreitzer H.Piringer I.Holzer W.Widhalm M. Helv. Chim. Acta 1998, 81: 2292 -
2e
White JD.Ruppert JF.Avery MA.Torii S.Nokami J. J. Am. Chem. Soc. 1981, 103: 1813 -
2f
Pati LC.Roy A.Mukherjee D. Tetrahedron 2002, 58: 1773 - 3
Mehta G.Srikrishna A. Chem. Rev. 1997, 97: 671 -
4a
Kocovsky P.Turecek F.Hajicek J. Synthesis of Natural Products: Problems of Selectivity Vol. 1: CRC Press; Boca Raton FL: 1986. Chap. 4. p.89 -
4b
Dalziel W.Hesp B.Stevenson KM.Jarvis JAJ. J. Chem. Soc., Perkin Trans. 1 1973, 2841 -
4c
.
Choudhary MI. Nat. Prod. Rep. 1999, 16: 619 -
5a
Thommen M.Keese R. Synlett 1997, 231 -
5b
Kuck D. Top. Curr. Chem. 1998, 196: 168 -
6a
Fitjer L.Klages U.Wehle D.Giersig M.Schormann N.Clegg W.Stephenson DS.Binsch G. Tetrahedron 1988, 44: 405 -
6b
Widjaja T.Fitjer L.Meindl K.Herbst-Irmer R. Tetrahedron 2008, 64: 4304 ; and references cited therein - 7
Fessner W.-D.Prinzbach H.Rihs C. Tetrahedron Lett. 1983, 24: 5857 - 8
Kuck D. Advances in Theoretically Interesting Molecules Vol. 4:Thummel RP. JAI Press; Greenwich CT: 1998. - 9
Dürr H.Gleiter R. Angew. Chem., Int. Ed. Engl. 1978, 17: 559 -
10a
Cox RJ. Non-Silver Photography Processes Academic Press; London: 1975. -
10b
Brown GH. Photochromism Wiley; New York: 1971. - 11
Feuerbacher N.Vögtle F.Windscheidt J.Poetsch E.Nieger M. Synthesis 1999, 117 - For reviews on the synthesis of spiro compounds, see:
-
12a
Krapcho AP. Synthesis 1978, 77 -
12b
Martin SF. Tetrahedron 1980, 36: 419 -
12c
Sannigrahi M. Tetrahedron 1999, 55: 9007 - 13
Posner GH.Hamill TG. J. Org. Chem. 1988, 53: 6031 - 14
Naik SN.Pandey B.Ayyangar NR. Synth. Commun. 1988, 18: 633 - 15
Sakata Y.Nakashima S.Goto Y.Tatemitsu H.Misumi S. J. Am. Chem. Soc. 1989, 111: 8979 - 16
Kotha S.Deb AC.Chattopadhyay S. Lett. Org. Chem. 2006, 3: 39 - 17
Huang H.Forsyth CJ. J. Org. Chem. 1995, 60: 2773 - 18
Canonne P.Boulanger R.Angers P. Tetrahedron Lett. 1991, 32: 5861 - 19
Venkatachalam M.Deshpande MN.Jawdosiuk M.Kubiak G.Wehrli S.Cook JM.Weiss U. Tetrahedron 1986, 42: 1597 - 20
Mori M.Kaneta N.Isono N.Shibasaki M. Tetrahedron Lett. 1991, 32: 6139 - 21
Bailey WF.Rossi K. J. Am. Chem. Soc. 1989, 111: 765 - 22
Sha C.-K.Lee F.-C.Lin H.-H. Chem. Commun. 2001, 39 - 23
Eilbracht P.Gersmeier A.Lennartz D.Huber T. Synthesis 1995, 330 - 24
Sattelkau T.Hollmann C.Eilbracht P. Synlett 1996, 1221 - 25
Bjørnstad V.Undheim K. Synthesis 2008, 962 - 26
Narayanan R.Swaminathan S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1990, 29: 401 - 27
Rajagopal D.Narayanan R.Swaminathan S. Tetrahedron Lett. 2001, 42: 4887 - 28
Lee TV.Cregg C. Synlett 1990, 317 - 29
Nieman JA.Parvez M.Keay BA. Tetrahedron: Asymmetry 1993, 4: 1973 - 30
Wendling F.Miesch M. Org. Lett. 2001, 3: 2689 - 31
Ciminale F.Lopez L.Farinola GM.Sportelli S. Tetrahedron Lett. 2001, 42: 5685 - 32
Molander GA.Harris CR. J. Am. Chem. Soc. 1995, 117: 3705 - 33
Kende AS.Roth B.Sanfilippo PJ. J. Am. Chem. Soc. 1982, 104: 1784 - 34
Wender PA.White AW. J. Am. Chem. Soc. 1988, 110: 2218 - 35
Swenton JS.Callinan A.Chen Y.Rohde JJ.Kerns ML.Morrow GW. J. Org. Chem. 1996, 61: 1267 - 36
Halterman RL.Vollhardt KPC.Welker ME.Bläser D.Boese R. J. Am. Chem. Soc. 1987, 109: 8105 - 37
Oh H.-S.Lee HI.Cha JK. Org. Lett. 2002, 4: 3707 - 38
Evans PA.Brandt TA. Tetrahedron Lett. 1996, 37: 1367 - 39
Villar JM.Delgado A.Llebaria A.Moretó JM.Molins E.Miravitlles C. Tetrahedron 1996, 52: 10525 - 40
Kondakov DY.Wang S.Negishi E. Tetrahedron Lett. 1996, 37: 3803 - 41
Trost BM.Lee DC.Rise F. Tetrahedron Lett. 1989, 30: 651 - 42
Trost BM.Shi Y. J. Am. Chem. Soc. 1991, 113: 701 - 43
Pearson AJ.Wang X. Tetrahedron Lett. 2002, 43: 7513 - 44
González JJ.García N.Gómez-Lor B.Echavarren AM. J. Org. Chem. 1997, 62: 1286 - 45
Muratake H.Natsume M.Nakai H. Tetrahedron 2004, 60: 11783 - 46
Shintani R.Park S.Hayashi T. J. Am. Chem. Soc. 2007, 129: 14866 - 47
Doi T.Iijima Y.Takasaki M.Takahashi T. J. Org. Chem. 2007, 72: 3667 - 48
Harrison TJ.Patrick BO.Dake GR. Org. Lett. 2007, 9: 367 - 49
D’yakonov VA.Finkelshtein ES.Ibragimov AG. Tetrahedron Lett. 2007, 48: 8583 - 50
Katz TJ.Gilbert AM.Huttenloch ME.Min-Min G.Brintzinger HH. Tetrahedron Lett. 1993, 34: 3551 - 51
Kuroda C.Hirono Y. Tetrahedron Lett. 1994, 35: 6895 - 52
Kuroda C.Koshio H. Chem. Lett. 2000, 962 - 53
Büchi G.Berthet D.Decorzant R.Grieder A.Hauser A. J. Org. Chem. 1976, 41: 3208 - 54
Hudlicky T.Radesca-Kuwart L.Li TQ.Bryant T. Tetrahedron Lett. 1988, 29: 3283 - 55
Kienzle F.Minder RE. Chimia 1985, 39: 100 - 56
Huang J.Frontier AJ. J. Am. Chem. Soc. 2007, 129: 8060 - 57
England DB.Merey G.Padwa A. Org. Lett. 2007, 9: 3805 - 58
Nakazaki A.Era T.Numada Y.Kobayashi S. Tetrahedron 2006, 62: 6264 - 59
Bach RD.Klix RC. Tetrahedron Lett. 1986, 27: 1983 - 60
Bach RD.Klix RC. J. Org. Chem. 1985, 50: 5438 - 61
Dake GR.Fenster MDB.Fleury M.Patrick BO. J. Org. Chem. 2004, 69: 5676 - 62
Hwu JR.Wetzel JM. J. Org. Chem. 1992, 57: 922 - 63
Wender PA.Ternansky RJ. Tetrahedron Lett. 1985, 26: 2625 - 64
Koft ER.Smith AB. J. Org. Chem. 1984, 49: 832 - 65
Caine D.Boucugnani AA.Chao ST.Dawson JB.Ingwalson PF. J. Org. Chem. 1976, 41: 1539 - 66
Provencal DP.Leahy JW. J. Org. Chem. 1994, 59: 5496 - 67
Dauben WG.Hart DJ. J. Am. Chem. Soc. 1977, 99: 7307 - 68
Corey EJ.Boger DL. Tetrahedron Lett. 1978, 19: 13 - 69
Srikrishna A.Vijaykumar D.Reddy TJ. Tetrahedron 1997, 53: 1439 - 70
Srikrishna A.Kumar PP. Tetrahedron 2000, 56: 8189 - 71
Kuck D.Seifert M. Chem. Ber. 1992, 125: 1461 - 72
Kuck D.Schuster A. Angew. Chem., Int. Ed. Engl. 1988, 27: 1192 - 73
Marx JN.Norman LR. J. Org. Chem. 1975, 40: 1602 - 74
Back TG.Payne JE. Org. Lett. 1999, 1: 663 - 75
Yang J.Cohn ST.Romo D. Org. Lett. 2000, 2: 763 -
76a
Kotha S.Manivannan E. J. Chem. Soc., Perkin Trans. 1 2001, 2543 -
76b
Kotha S.Brahmachary E.Lahiri K. Eur. J. Org. Chem. 2005, 4741 -
77a
Goldberg DR.Hansen JA.Giguere RJ. Tetrahedron Lett. 1993, 34: 8003 -
77b
Brodney MA.O’Leary JP.Hansen JA.Giguere RJ. Synth. Commun. 1995, 25: 521 - 78
Knölker H.-J.Jones PG.Graf R. Synlett 1996, 1155 - 79
Moser WH.Zhang J.Lecher CS.Frazier TL.Pink M. Org. Lett. 2002, 4: 1981 - 80
Knölker H.-J.Baum E.Graf R.Jones PG.Spieß O. Angew. Chem. Int. Ed. 1999, 38: 2583 - 81
Klimova EI.García MM.Klimova T.Toledano CA.Toscano RA.Ramírez LR. J. Organomet. Chem. 2002, 649: 86 - 82
Klimova EI.García MM.Klimova T.Ortega SH.Bakinovsky LV. Org. Biomol. Chem. 2003, 1: 1210 - 83
Dohi T.Maruyama A.Yoshimura M.Morimoto K.Tohma H.Kita Y. Angew. Chem. Int. Ed. 2005, 44: 6193 - 84
Mahandru GM.Skauge ARL.Chowdhury SK.Amarasinghe KKD.Heeg MJ.Montgomery J. J. Am. Chem. Soc. 2003, 125: 13481 - 85
Saeed M.Rogan E.Cavalieri E. Tetrahedron Lett. 2005, 46: 4449 -
86a
Mikami K.Yusa Y.Hatano M.Wakabayashi K.Aikawa K. Tetrahedron 2004, 60: 4475 -
86b
Mikami K.Yusa Y.Hatano M.Wakabayashi K.Aikawa K. Chem. Commun. 2004, 98 - 87
Bialy SAAE.Braun H.Tietze LF. Angew. Chem. Int. Ed. 2004, 43: 5391 - 88
Tietze LF.Steck PL. Eur. J. Org. Chem. 2001, 4353 - 89
Pizzirani D.Roberti M.Recanatini M. Tetrahedron Lett. 2007, 48: 7120 - 90
Shanmugam P.Srinivasan R.Rajagopalan K. Tetrahedron 1997, 53: 11685 - 91
Clive DLJ.Tao Y.Khodabocus A.Wu Y.-J.Angoh AG.Bennett SM.Boddy CN.Bordeleau L.Kellner D.Kleiner G.Middleton DS.Nichols CJ.Richardson SR.Vernon PG. J. Am. Chem. Soc. 1994, 116: 11275 - 92
Curran DP.Kuo S.-C. J. Am. Chem. Soc. 1986, 108: 1106 - 93
Beaufils F.Dénès F.Becattini B.Renaud P.Schenk K. Adv. Synth. Catal. 2005, 347: 1587 - 94
Inui M.Nakazaki A.Kobayashi S. Org. Lett. 2007, 9: 469 - 95
Sha C.-K.Lee F.-K.Chang C.-J. J. Am. Chem. Soc. 1999, 121: 9875 - 96
Taniguchi T.Tanabe G.Muraoka O.Ishibashi H. Org. Lett. 2008, 10: 197 - 97
Lemieux RM.Devine PN.Mechelke MF.Meyers AI. J. Org. Chem. 1999, 64: 3585 - 98
Hammer K.Undheim K. Tetrahedron 1997, 53: 2309 - 99
Bassindale MJ.Hamley P.Leitner A.Harrity JPA. Tetrahedron Lett. 1999, 40: 3247 -
100a
Kotha S.Manivannan E.Ganesh T.Sreenivasachary N.Deb A. Synlett 1999, 1618 -
100b
Kotha S.Sreenivasachary N. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001, 40: 763 - 101
Bassindale MJ.Edwards AS.Hamley P.Adams H.Harrity JPA. Chem. Commun. 2000, 1035 - 102
Wallace DJ.Goodman JM.Kennedy DJ.Davies AJ.Cowden CJ.Ashwood MS.Cottrell IF.Dolling U.-H.Reider PJ. Org. Lett. 2001, 3: 671 - 103
Wright DL.Schulte JP.Page MA. Org. Lett. 2000, 2: 1847 - 104
Kotha S.Deb AC. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2008, 47: 1120 - 105
Kotha S.Manivannan E. ARKIVOC 2003, (iii): 67 - 106
Kotha S.Deb AC.Kumar RV. Bioorg. Med. Chem. Lett. 2005, 15: 1039 -
107a
Schobert R.Urbina-González JM. Tetrahedron Lett. 2005, 46: 3657 -
107b
Srikrishna A.Rao MS.Gharpure SJ.Babu NC. Synlett 2001, 1986 -
107c
Sabitha G.Reddy ChS.Babu RS.Yadav JS. Synlett 2001, 1787 -
107d
Gurjar MK.Ravindranadh SV.Karmakar S. Chem. Commun. 2001, 241 -
108a
Deb AC. Ph.D. Thesis IIT-Bombay; India: 2004. -
108b
Kotha S.Lahiri K. Synlett 2007, 2767 -
109a
Kotha S.Mandal K. Tetrahedron Lett. 2004, 45: 1391 -
109b
Green J.McHale D. Chem. Ind. (London) 1964, 1801 - For selected examples of spiroannulation, see:
-
110a
Undheim K.Efskind J. Tetrahedron 2000, 56: 4847 -
110b
Maier ME.Bugl M. Synlett 1998, 1390 -
110c
van Hooft PAV.Leeuwenburgh MA.Overkleeft HS.van der Marel GA.van Boeckel CAA.van Boom JH. Tetrahedron Lett. 1998, 39: 6061 -
110d
Hammer K.Undheim K. Tetrahedron 1997, 53: 10603 -
110e
Undheim K. Amino Acids 2008, 34: 357 -
110f
Mioara A.Undheim K. Tetrahedron: Asymmetry 2004, 15: 53 - 111
Kotha S.Mandal K.Tiwari A.Mobin SM. Chem. Eur. J. 2006, 12: 8024 - 112
Arjona O.Csákÿ AG.Plumet J. Eur. J. Org. Chem. 2003, 611 - 113
Veretenov AL.Smit WA.Vorontsova LG.Kurella MG. Tetrahedron Lett. 1991, 32: 2109 - 114
Kerr WJ.McLaughlin M.Morrison AJ.Pauson PL. Org. Lett. 2001, 3: 2945 - 115
Knudsen MJ.Schore NE. J. Org. Chem. 1984, 49: 5025 - 116
de Meijere A.Becker H.Stolle A.Kozhushkov SI.Bes MT.Salaün J.Noltemeyer M. Chem. Eur. J. 2005, 11: 2471 - 117
van der Waals A.Keese R. J. Chem. Soc., Chem. Commun. 1992, 570 - 118
Lee SI.Son SU.Choi MR.Chung YK.Lee S.-G. Tetrahedron Lett. 2003, 44: 4705 - 119
Hudlicky T.Reed JW. The Way of Synthesis Wiley-VCH; Weinheim: 2007. p.98